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When the Web Was Actively Trying to Kill You: A Field Guide to Early Front-End Lore
In the ongoing retrospective series I have kicked off on LinkedIn and YouTube about the maturation of the web platform, I am going to be focusing on how Boston and Cambridge served as ground zero for modern front-end engineering between 2008 and 2013. We will talk about the launch of HTML5 Boilerplate, the transition to…
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TypeScript Won. Now It’s Giving Up Its Superpowers.
When you spin up a greenfield project on a Tuesday afternoon, a build step feels like a completely reasonable trade-off. You install a bundler, configure a transpiler, sprinkle in a few TypeScript-specific conveniences, and marvel at the developer ergonomics. Having the compiler quietly invent runtime JavaScript out of thin air to support an enum, a…
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The Superset Trap: Why Node’s Native TypeScript is Going to Break Enterprise Brains
If you spend your time in open-source mailing lists or arguing about AST transformations on social media, the recent push toward “erasable syntax” makes total sense. I’ve been a proponent of TypeScript for a long time. In the early days, whenever someone brought up enum, for example, I remember having conversations along the lines of:…
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Governing the Generative Drift: Why We Need the Assumptions & Constraints Manifest (ACM)
A couple of weeks ago, I talked about the “Happy Path Trap”—how LLMs create massive Day 1 velocity while burying teams in silent Day 2 architectural debt. During that discussion, I pitched an idea: What if we required an Assumptions & Constraints Manifest (ACM) in every AI-assisted PR to make hidden trade-offs visible? Since I’m…
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Weekly Web Dev Quick Hits
A couple quick hits while I rev the content engine back up over here! CSS Weaponized at Black Hat 2026: Security researcher Gareth Heyes dropped a research paper showing how CSS alone can break out of webmail sanitizers. Without a single line of JavaScript, malicious stylesheets in Gmail and Outlook were manipulated to spoof UI…